Reddington has the ability to keep everyone guessing on The Blacklist. Sometimes he surprises fans in a positive way and, other times, a negative way.

Much of the television show The Blacklist centers on the infamous criminal Raymond Reddington (James Spader). Reddington is a dynamic and complex criminal. While he commits many awful atrocities, he also seems to operate under a very specific moral code.

This character has the ability to keep everyone guessing. Sometimes he surprises fans in a positive way and other times he surprises fans in a negative way. Here are 5 times we felt bad for Raymond Reddington and 5 times we hated him!

Hated: Treatment Of Glenn

The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)
The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)

Glenn is one of Reddington’s most loyal associates. Though plans involving Glenn don’t always go as smoothly as they could, he always gets the job done. Reddington regularly relies on Glenn to accomplish some of his more complicated tasks, yet he isn’t always kind to Glenn.

He hurtles many insults and Glenn and regularly undermines him and questions his ability to complete the jobs. If he is unhappy with the quality of Glenn’s work, he could find someone else to assist him. If not, he should consider being a little kinder – especially considering how difficult it can be to find someone as loyal as Glenn.

Felt Bad: Naomi In Danger

The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)
The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)

Reddington’s past and identity are somewhat of a mystery. One thing that is clear is that he cared deeply for Naomi – who it is assumed he was married to at one point in time. Due to her previous relationship with Reddington, Naomi has to go into hiding.

When Naomi’s location is discovered and she is put in harm’s way again, Reddington clearly feels responsible. This is one moment where Reddington’s compassion and love for others shows as it is clear he never wanted to do anything to endanger her.

Hated: Helped Samar Run Away

The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)
The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)

Samar and Aram had a beautiful relationship. When Samar’s health began to decline, she was determined not to be a burden on anyone. She lied to Aram and made him believe they were going to run away together. She then reached out to Reddington, leaving without saying goodbye.

While his desire to help and respect Samar’s wishes is noble, robbing Aram a chance to say goodbye seems cruel. This decision sent Amar down a truly dark path and fans couldn’t help but feel heartbroken watching him struggle. Seeing Amar fall apart made it difficult not to hate Reddington in that moment.

Felt Bad: Katarina Stabs Him

The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)
The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)

Another big mystery of the show surrounds the history between Reddington and Katarina. Whoever Red is, it always seemed as though he did his best to protect Katarina and deflect attention off of her.

He then decides to meet her as she is someone he seemingly trusts. However, when he gets there, Katarina stabs him. This is a shock to both viewers and Reddington and fans couldn’t help but feel bad as he lay there bleeding on the sidewalk.

Hated: Killed Sam

The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)
The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)

Sam and Reddington had a close friendship that had lasted for many years. When Sam falls ill and is nearing the end of his life, Reddington goes to visit him. While he is there, he discovers that Sam – who has raised Liz since she was young and seemingly knows the truth about Reddington – has decided he would like to come clean before he dies.

Upon expressing his desire to be honest with Liz, Reddington kills him. While Sam didn’t have long to live, it was still wrong of Reddington to rob Liz of her chance to say goodbye to her father and to learn the truth that has been hidden from her for so long.

Felt Bad: Passes Out

The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)
The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)

For a while now, the show has been hinting that something is wrong with Reddington. He has been shown secretly meeting with doctors and injecting himself with some kind of medication. Still, viewers were given little insight into what exactly is causing Red to seek treatment.

At the end of the recent episode “Nyle Hatcher”, Reddington’s health seems to have finally taken a turn for the worse. Dembe discovers Reddington on the floor after he collapses. It is unclear how this will affect him moving forward, but is clear that something is very wrong.

Hated: Dragging Ilya Into Danger

The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)
The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)

Though it is unclear exactly how Ilya and Reddington are connected, it is clear that they both care for each other. From what we have seen of Ilya, he seems to be a decent guy who has moved on from his past. He has a loving wife and has lived a normal life for many decades.

When Dom lies to Liz saying that Reddington is really Ilya in disguise, Ilya is dragged into a dangerous situation. Though it wasn’t originally Reddington’s plan to include Ilya, he allowed this to continue. This ended up uprooting Ilya’s life. He was captured and tortured by Katarina and his mental health deteriorated. Watching the pain and suffering his wife and him have endured due to Reddington’s recklessness is infuriating.

Felt Bad: Thinks Liz Is Dead

The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)
The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)

It is clear that the person Reddington cares for above all others is Liz. When Elizabeth is pregnant with her child, she decides she needs to escape the dangers of her life. She plans to go into hiding to raise her child safely with her husband Tom.

Reddington believes that Liz is dead and is distraught. His pain is palpable and difficult to watch. This brought back some difficult memories for Reddington as he blamed himself for Liz’s death and reflected on some of his past mistakes. Believing Liz was dead was one of Reddington’s lowest moments.

Hated: Killed Kaplan

The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)
The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)

Mr. Kaplan was one of the most developed and beloved supporting characters in The Blacklist. She had been a loyal associate of Reddington’s for a long time. When Mr. Kaplan’s backstory revealed that she had originally had a connection with Katarina and had helped to raise Liz as a child, fans were shocked.

Fans were even more surprised to discover that Liz wasn’t actually dead. In fact, Kaplan had helped arrange her disappearance so she could live a safe life. Reddington did not take well to this betrayal and a battle between him and Kate ensued. This war ended with him killing Kate – the most unforgivable wrongdoing Reddington has ever carried out.

Felt Bad: Liz And Tom Dying In Car

The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)
The Blacklist: 5 Times We Felt Bad For Reddington (& 5 Times We Hated Him)

One of the most heartbreaking moments in the entire series is when Tom and Liz almost die. As Dembe rushes them both to the hospital in the back of his car, the two profess their love to each other. As they share this intimate moment, both aware that they could die at any second, Red is forced to look on with panic in his eyes.

At this moment, Reddington is powerless. His lack of control and inability to protect Liz is the worst possible situation. When watching this scene, there are sure to be many tears.

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